spiraeoside

2-[4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one

CAS: 20229-56-5 C21 H20 C12 MW: 416.52240000

Identification

Namespiraeoside
IUPAC3,5,7-trihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
CAS Number20229-56-5
EINECS243-614-6
FDA UNIIK2B74751XI
Molecular FormulaC21 H20 C12
Molecular Weight416.52240000
MDL NumberMFCD00221723
Nikkaji NumberJ94.563C

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 835.60 °C. @ 760.00 mm Hg (est)
Flash Point 562.00 °F. TCC ( 294.70 °C. ) (est)
logP (o/w) -0.380 (est)
Soluble in water, 2.159e+004 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic ingredient for skin conditioning
Recommendation for spiraeoside usage levels up tonot for fragrance use.
Recommendation for spiraeoside flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cherry sweet cherry filipendula ulmaria flower onion onion bulb onion epidermis

Synonyms

4H-1- benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-trihydroxy- 2-(4-(beta-D- glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one 2-[4-(beta-D- glucopyranosyloxy)-3-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one quercetin 4'-O-glucoside spiraein spiraeosid 3,5,7- trihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one PubMed: A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia. PubMed: Relationship analysis between flavonoids structure and subcritical water extraction (SWE). PubMed: Polyphenol contents and antioxidant activities of extracts from flowers of two Crataegus azarolus L. varieties. PubMed: Spiraeosides A and B, two new diterpenoid glucosides from Spiraea japonica var. ovalifolia. PubMed: The crystal structure of human cytosolic beta-glucosidase unravels the substrate aglycone specificity of a family 1 glycoside hydrolase. PubMed: Antioxidant activity of Filipendula hexapetala flowers. PubMed: Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones. PubMed: Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT? PubMed: Disposition and metabolism of [2-14C]quercetin-4'-glucoside in rats. PubMed: In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer. PubMed: Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans. PubMed: Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum. PubMed: The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. PubMed: Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation. PubMed: Absorption of quercetin-3-glucoside and quercetin-4'-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. PubMed: Determination of flavonol metabolites in plasma and tissues of rats by HPLC-radiocounting and tandem mass spectrometry following oral ingestion of [2-(14)C]quercetin-4'-glucoside. PubMed: Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide. PubMed: Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4'-glucoside. PubMed: Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2. PubMed: Pharmacokinetics and bioavailability of quercetin glycosides in humans. PubMed: Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1). PubMed: Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. PubMed: Quercetin glucosides are completely hydrolyzed in ileostomy patients before absorption. PubMed: Cellular uptake of dietary flavonoid quercetin 4'-beta-glucoside by sodium-dependent glucose transporter SGLT1. PubMed: Efflux of dietary flavonoid quercetin 4'-beta-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance-associated protein-2. PubMed: Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. PubMed: Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. PubMed: The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. PubMed: Absorption and excretion of conjugated flavonols, including quercetin-4'-O-beta-glucoside and isorhamnetin-4'-O-beta-glucoside by human volunteers after the consumption of onions. PubMed: Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity. PubMed: Dietary quercetin glycosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells. PubMed: Absorption and disposition kinetics of the dietary antioxidant quercetin in man. PubMed: Densitometric evaluation of spiraeoside after derivatization in flowers of Filipendula ulmaria (L.) Maxim. PubMed: Induction of sister-chromatid exchanges (SCE), polyploidy, and micronuclei by plant flavonoids in human lymphocyte cultures. A comparative study of 19 flavonoids. PubMed: On the Occurrence of Kaempferol-4'-O-beta-D-glucopyranoside in Filipendula ulmaria and Allium cepa. PubMed: [Flavonols and flavones of vegetables. VI. On the changes of the flavonols of onions (authors transl)]. PubMed: [Flavonols and flavones of vegetables. VII. Flavonols of leek, chive and garlic (author's transl)].